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Journal of Endotoxin Research
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Synthesis of Kdo-trisaccharide derivatives of chlamydial and enterobacterial LPS containing carboxyl-reduced or β-configurated Kdo-residues

P. Kosma

Department of Chemistry, University of Agriculture, Vienna, Austria, Forschungsinstitut Borstel, Borstel, Germany

F.W. D'Souza

Department of Chemistry, University of Agriculture, Vienna, Austria, Forschungsinstitut Borstel, Borstel, Germany

H. Brade

Department of Chemistry, University of Agriculture, Vienna, Austria, Forschungsinstitut Borstel, Borstel, Germany

Five allyl glycosides corresponding to the 3-deoxy-D-manno-2-octulosonic acid (Kdo) containing genus-specific LPS epitope of Chlamydia were synthesized. Compounds 5 and 22 contain one carboxyl-reduced Kdo moiety linked to O-4 of the proximal Kdo unit, whereas the analogues 28, 34 and 36 each contain one β-linked Kdo-residue within the trisaccharide sequence Kdo p-(2->8)-Kdop-(2->4)-Kdop. Elaboration of the carboxyl-reduced derivatives was achieved by BF3•Et2O-catalyzed coupling of Kdo-fluoride derivatives 1 or 14 with the 7,8-O-carbonyl-derivative 2. The β-linked oligosaccharides were obtained by Helferich-glycosidation of the respective Kdo-disaccharide bromide derivatives 26 and 31. The deprotected compounds - characterized by H and 13C NMR spectroscopy - are suitable haptens for the immunochemical study of monoclonal antibodies directed against the Kdo-region of chlamydial and enterobacterial LPS.

Journal of Endotoxin Research, Vol. 2, No. 1, 63-76 (1995)
DOI: 10.1177/096805199500200108
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